{"title":"2-羟丙基-β-环糊精R-和s -酮洛芬包合物的光谱研究","authors":"Asma Obaid, Nujud Maslamani, Ameerah Theqah, Hind Siddiq, Reem Ghubayra, Ibtisam Mousa, Arniza Khairani Mohd Jamil, Siti Munirah Saharin, Sharifah Mohamad","doi":"10.1002/chir.70045","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>Ketoprofen, also known as (RS)-2-(3-benzoylphenyl)-propionic acid, has the molecular formula C<sub>16</sub>H<sub>14</sub>O<sub>3</sub> and is classified as a non-steroidal anti-inflammatory medication. R-ketoprofen has stronger analgesic effects than S-K, and as a result, there is a growing interest in enantio-recognition research, which may be accomplished through supramolecular interactions, particularly host-guest reactions. A 1:1 molar ratio was used to produce the combination of separate RK and SK and a 0.01 M stock solution of HP-β-CD to get the final concentration of 6 × 10<sup>−4</sup> M. Ethanol was used to make stock solutions of ketoprofen enantiomers (1 mM). Researchers combined a specific volume of ketoprofen with 2-hydroxypropyl-beta-cyclodextrin (HPβ-CD) and then used spectroscopic methods to study how the S-ketoprofen (SK) and R-ketoprofen (RK) enantiomers interact with HPβ-CD to form inclusion complexes in an aqueous solution. The Benesi–Hildebrand plot was used to determine the inclusion complexes' stoichiometry ratio and binding constant; both enantiomers displayed a 1:1 stoichiometry ratio inclusion complex with HP-β-CD. Compared with SK (799 M<sup>−1</sup>), RK has a higher binding constant (1038 M<sup>−1</sup>). These results showed that HP-β-CD preferred to form inclusion complexes with RK over SK. At neutral pH, there are significant differences between RK and SK when HP-β-CD is present.</p>\n </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 8","pages":""},"PeriodicalIF":3.0000,"publicationDate":"2025-08-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Spectroscopic Study of R- and S-Ketoprofen Inclusion Complexes With 2-Hydroxypropyl-β-cyclodextrin\",\"authors\":\"Asma Obaid, Nujud Maslamani, Ameerah Theqah, Hind Siddiq, Reem Ghubayra, Ibtisam Mousa, Arniza Khairani Mohd Jamil, Siti Munirah Saharin, Sharifah Mohamad\",\"doi\":\"10.1002/chir.70045\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>Ketoprofen, also known as (RS)-2-(3-benzoylphenyl)-propionic acid, has the molecular formula C<sub>16</sub>H<sub>14</sub>O<sub>3</sub> and is classified as a non-steroidal anti-inflammatory medication. R-ketoprofen has stronger analgesic effects than S-K, and as a result, there is a growing interest in enantio-recognition research, which may be accomplished through supramolecular interactions, particularly host-guest reactions. A 1:1 molar ratio was used to produce the combination of separate RK and SK and a 0.01 M stock solution of HP-β-CD to get the final concentration of 6 × 10<sup>−4</sup> M. Ethanol was used to make stock solutions of ketoprofen enantiomers (1 mM). Researchers combined a specific volume of ketoprofen with 2-hydroxypropyl-beta-cyclodextrin (HPβ-CD) and then used spectroscopic methods to study how the S-ketoprofen (SK) and R-ketoprofen (RK) enantiomers interact with HPβ-CD to form inclusion complexes in an aqueous solution. The Benesi–Hildebrand plot was used to determine the inclusion complexes' stoichiometry ratio and binding constant; both enantiomers displayed a 1:1 stoichiometry ratio inclusion complex with HP-β-CD. Compared with SK (799 M<sup>−1</sup>), RK has a higher binding constant (1038 M<sup>−1</sup>). These results showed that HP-β-CD preferred to form inclusion complexes with RK over SK. At neutral pH, there are significant differences between RK and SK when HP-β-CD is present.</p>\\n </div>\",\"PeriodicalId\":10170,\"journal\":{\"name\":\"Chirality\",\"volume\":\"37 8\",\"pages\":\"\"},\"PeriodicalIF\":3.0000,\"publicationDate\":\"2025-08-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chirality\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/chir.70045\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ANALYTICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chirality","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/chir.70045","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ANALYTICAL","Score":null,"Total":0}
Spectroscopic Study of R- and S-Ketoprofen Inclusion Complexes With 2-Hydroxypropyl-β-cyclodextrin
Ketoprofen, also known as (RS)-2-(3-benzoylphenyl)-propionic acid, has the molecular formula C16H14O3 and is classified as a non-steroidal anti-inflammatory medication. R-ketoprofen has stronger analgesic effects than S-K, and as a result, there is a growing interest in enantio-recognition research, which may be accomplished through supramolecular interactions, particularly host-guest reactions. A 1:1 molar ratio was used to produce the combination of separate RK and SK and a 0.01 M stock solution of HP-β-CD to get the final concentration of 6 × 10−4 M. Ethanol was used to make stock solutions of ketoprofen enantiomers (1 mM). Researchers combined a specific volume of ketoprofen with 2-hydroxypropyl-beta-cyclodextrin (HPβ-CD) and then used spectroscopic methods to study how the S-ketoprofen (SK) and R-ketoprofen (RK) enantiomers interact with HPβ-CD to form inclusion complexes in an aqueous solution. The Benesi–Hildebrand plot was used to determine the inclusion complexes' stoichiometry ratio and binding constant; both enantiomers displayed a 1:1 stoichiometry ratio inclusion complex with HP-β-CD. Compared with SK (799 M−1), RK has a higher binding constant (1038 M−1). These results showed that HP-β-CD preferred to form inclusion complexes with RK over SK. At neutral pH, there are significant differences between RK and SK when HP-β-CD is present.
期刊介绍:
The main aim of the journal is to publish original contributions of scientific work on the role of chirality in chemistry and biochemistry in respect to biological, chemical, materials, pharmacological, spectroscopic and physical properties.
Papers on the chemistry (physiochemical, preparative synthetic, and analytical), physics, pharmacology, clinical pharmacology, toxicology, and other biological aspects of chiral molecules will be published.